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CHE 118B: Organic Chemistry > Midterm 1 MPS > Flashcards

Midterm 1 MPS Flashcards

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1
Q

CH. 12 Recommended Probs

65a

A

See CH.12 Rec. Problem Solutions

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2
Q

CH. 12 Recommended Probs

45o

A

See CH.12 Rec. Problem Solutions

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3
Q

Give the HNMR chemical shift range typical of this FG

Iodoalkane

A

3.1-3.3 ppm

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4
Q

There is a “gap” at around 5.2 ppm in HNMR of alkenes where there is little to no activity. What is important about this “gap”?

A

This “gap” can be used to determine if an alkene is internal or terminal.

Since H’s attached to the terminal end of alkenes have a ppm shift of 4.6-5.2 ppm, you can assume that any signals to the left of this gap are H’s attached to the terminal end of an alkene (and thus, that the alkene is terminal).

Since H’s attached to the internal end of of alkenes have a ppm shift of 5.2-6.0 ppm, you can assume that any signals to the right of this gap are H’s attached to the internal end of an alkene.

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4
Q

CH. 11 Recommended Problems

30c

A

See CH. 11 Recommended Probs Key

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5
Q

SP2010 MT1

2i

A

See key

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6
Q

See Properties of Alkenes & pi-bonds

2

A

See key

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7
Q

SP2010 MT1

3g

A

See key

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8
Q

See NMR Practice Problems

15

A

See key

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8
Q

See NMR Practice Problems

23

A

See key

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8
Q

CH. 12 Recommended Probs

45e

A

See CH.12 Rec. Problem Solutions

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8
Q

CH. 12 Recommended Probs

64b

A

See CH.12 Rec. Problem Solutions

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8
Q

SP2013 MT1

7d

A

See solutions

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9
Q

Give the HNMR chemical shift range typical of this FG

Bromoalkane

A

3.4-3.6 ppm

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10
Q

CH. 11 Recommended Problems

30d

A

See CH. 11 Recommended Probs Key

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11
Q

Give the HNMR chemical shift range typical of this FG

Chloroalkane

A

3.6-3.8 ppm

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11
Q

CH. 12 Recommended Probs

49m

A

See CH.12 Rec. Problem Solutions

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11
Q

CH. 12 Recommended Probs

49o

A

See CH.12 Rec. Problem Solutions

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11
Q

CH. 12 Recommended Probs

60b

A

See CH.12 Rec. Problem Solutions

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11
Q

CH. 11 Recommended Problems

29d

A

See CH. 11 Recommended Probs Key

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11
Q

CH. 11 Recommended Problems

37c

A

See CH. 11 Recommended Probs Key

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11
Q

Workshop Spectroscopy Practice #1-26

26

A

See key

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11
Q

Alicia PS #1

2c

A

See key

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13
Q

CH. 12 Recommended Probs

44b

A

See CH.12 Rec. Problem Solutions

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14
Q

Workshop Spectroscopy Practice #1-26

11

A

See key

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15
Q

CH. 12 Recommended Probs

57a

A

See CH.12 Rec. Problem Solutions

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15
Q

CH. 12 Recommended Probs

57b

A

See CH.12 Rec. Problem Solutions

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15
Q

CH. 11 Recommended Problems

37e

A

See CH. 11 Recommended Probs Key

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16
Q

See Properties of Alkenes & pi-bonds

1

A

See key

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17
Q

SP2013 MT1

2b

A

See solutions

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18
Q

What is the IR wavenumber range for Aromatics?

A

~3030 cm-1

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18
Q

What is the IR wavenumber range for -CC- Alkynes?

A

2100-2260 cm-1

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18
Q

Give the HNMR chemical shift range typical of this FG

Aromatic (Benzene-H)

A

6.5-9.5 ppm, usually 7-8 ppm

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18
Q

CH. 12 Recommended Probs

42a

A

See CH.12 Rec. Problem Solutions

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19
Q

CH. 12 Recommended Probs

46j

A

See CH.12 Rec. Problem Solutions

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20
Q

CH. 12 Recommended Probs

49c

A

See CH.12 Rec. Problem Solutions

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21
Q

See NMR Practice Problems

19

A

See key

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21
Q

CH. 12 Recommended Probs

64a

A

See CH.12 Rec. Problem Solutions

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21
Q

SP2010 MT1

1a

A

See key

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21
Q

SP2010 MT1

2h

A

See key

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22
Q

CH. 12 Recommended Probs

59b

A

See CH.12 Rec. Problem Solutions

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23
Q

Alcohol (-OH)

For the above FG, give the following:

  1. Wavenumber range
  2. Signal characteristics (strong, broad, sharp, etc)
A
  1. 3400-3650 cm-1
  2. Broad, strong
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23
Q

CH. 11 Recommended Problems

30i

A

See CH. 11 Recommended Probs Key

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24
Q

CH. 11 Recommended Problems

55a

A

See CH. 11 Recommended Probs Key

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25
Q

CH. 12 Recommended Probs

41a

A

See CH.12 Rec. Problem Solutions

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25
Q

CH. 12 Recommended Probs

49f

A

See CH.12 Rec. Problem Solutions

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25
Q

CH. 12 Recommended Probs

53e

A

See CH.12 Rec. Problem Solutions

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25
Q

CH. 12 Recommended Probs

57c

A

See CH.12 Rec. Problem Solutions

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25
Q

CH. 11 Recommended Problems

66b

A

See CH. 11 Recommended Probs Key

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26
Q

CH. 11 Recommended Problems

31b

A

See CH. 11 Recommended Probs Key

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27
Q

Alicia PS #1

4

A

See key

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28
Q

Give the HNMR chemical shift range typical of this FG

Next to aromatic (Benzene-CH)

A

2.2-2.5 ppm

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28
Q

Workshop Spectroscopy Practice #1-26

19

A

See key

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29
Q

CH. 12 Recommended Probs

45p

A

See CH.12 Rec. Problem Solutions

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30
Q

CH. 12 Recommended Probs

34

A

See CH.12 Rec. Problem Solutions

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30
Q

CH. 11 Recommended Problems

33

A

See CH. 11 Recommended Probs Key

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30
Q

Alicia PS #1

1b

A

See key

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30
Q

Alicia PS #1

2e

A

See key

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30
Q

SP2013 MT1

3b

A

See solutions

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30
Q

SP2013 MT1

3h

A

See solutions

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30
Q

SP2010 MT1

3e

A

See key

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31
Q

See Alkene Nomenclature PS

16

A

See key

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32
Q

CH. 11 Recommended Problems

41g

A

See CH. 11 Recommended Probs Key

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33
Q

CH. 11 Recommended Problems

51a

A

See CH. 11 Recommended Probs Key

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34
Q

CH. 11 Recommended Problems

29b

A

See CH. 11 Recommended Probs Key

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35
Q

CH. 11 Recommended Problems

43

A

See CH. 11 Recommended Probs Key

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36
Q

Give the HNMR chemical shift range typical of this FG

Ester

A

3.5-4.5 ppm

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36
Q

SP2010 MT1

1f

A

See key

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36
Q

SP2010 MT1

9

A

See key

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37
Q

CH. 11 Recommended Problems

34c

A

See CH. 11 Recommended Probs Key

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38
Q

SP2010 MT1

7c

A

See key

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39
Q

Workshop Spectroscopy Practice #1-26

2

A

See key

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40
Q

CH. 11 Recommended Problems

51e

A

See CH. 11 Recommended Probs Key

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41
Q

See NMR Practice Problems

3

A

See key

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41
Q

CH. 12 Recommended Probs

66b

A

See CH.12 Rec. Problem Solutions

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41
Q

CH. 11 Recommended Problems

55c

A

See CH. 11 Recommended Probs Key

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42
Q

CH. 12 Recommended Probs

39

A

See CH.12 Rec. Problem Solutions

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44
Q

CH. 11 Recommended Problems

55b

A

See CH. 11 Recommended Probs Key

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45
Q

CH. 11 Recommended Problems

51f

A

See CH. 11 Recommended Probs Key

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46
Q

Workshop Spectroscopy Practice #1-26

23

A

See key

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47
Q

CH. 12 Recommended Probs

40c

A

See CH.12 Rec. Problem Solutions

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47
Q

CH. 12 Recommended Probs

46d

A

See CH.12 Rec. Problem Solutions

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47
Q

CH. 11 Recommended Problems

34d

A

See CH. 11 Recommended Probs Key

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47
Q

Alicia PS #1

5

A

See key

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48
Q

See NMR Practice Problems

13

A

See key

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49
Q

CH. 12 Recommended Probs

58b

A

See CH.12 Rec. Problem Solutions

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50
Q

CH. 11 Recommended Problems

32a

A

See CH. 11 Recommended Probs Key

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51
Q

SP2013 MT1

3a

A

See solutions

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53
Q

SP2013 MT1

1f

A

See solutions

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54
Q

Give the HNMR chemical shift range typical of this FG

Ether/Alcohol

A

3.3-4.0 ppm

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54
Q

CH. 12 Recommended Probs

62

A

See CH.12 Rec. Problem Solutions

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56
Q

See NMR Practice Problems

22

A

See key

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57
Q

What is the IR wavenumber range for C=C benzene double bonds?

A

1660-2000 cm-1 and 1450-1600 cm-1

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58
Q

CH. 11 Recommended Problems

37d

A

See CH. 11 Recommended Probs Key

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59
Q

See Alkene Nomenclature PS

6

A

See key

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60
Q

See Alkene Nomenclature PS

12

A

See key

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61
Q

Give the coupling constant (J) and coupling pattern for geminal, trans-vicinal, cis-vicinal, allylic and alkane H-coupling.

A
  • Geminal: 0-3 Hz; doublet (d)
  • trans-vicinal: 10-18 Hz, usually ~16 Hz; doublet (d)
  • cis-vicinal: 6-14 Hz, usually ~10 Hz; doublet (d)
  • Allylic: 0-3 Hz; doublet (d), triplet (t) or quartet (q)
  • Alkane: 4-10 Hz, usually ~7 Hz; doublet (d), triplet (t), or quartet (q)
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63
Q

CH. 12 Recommended Probs

50

A

See CH.12 Rec. Problem Solutions

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64
Q

SP2013 MT1

4

A

See solutions

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65
Q

Alicia PS #1

2b

A

See key

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66
Q

CH. 12 Recommended Probs

42c

A

See CH.12 Rec. Problem Solutions

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68
Q

See NMR Practice Problems

11

A

See key

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69
Q

Explain what the fragmentation obtained from mass spectrometry is, and why it is important?

A
  • When atoms are deflected, they can create fragments of the compound.
  • Some fragments are harder to make than others; but are usually made in specific ratios.
  • These ratios of framentation can be used as a “fingerprint” for the compound, and are important in identifying unknown compounds.
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70
Q

CH. 12 Recommended Probs

59a

A

See CH.12 Rec. Problem Solutions

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71
Q

CH. 11 Recommended Problems

61a

A

See CH. 11 Recommended Probs Key

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72
Q

CH. 12 Recommended Probs

45a

A

See CH.12 Rec. Problem Solutions

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72
Q

CH. 11 Recommended Problems

27

A

See CH. 11 Recommended Probs Key

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72
Q

SP2010 MT1

3d

A

See key

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73
Q

CH. 12 Recommended Probs

42f

A

See CH.12 Rec. Problem Solutions

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74
Q

CH. 12 Recommended Probs

63c

A

See CH.12 Rec. Problem Solutions

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75
Q

CH. 11 Recommended Problems

63f

A

See CH. 11 Recommended Probs Key

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76
Q

SP2010 MT1

3c

A

See key

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77
Q

Workshop Spectroscopy Practice #1-26

8

A

See key

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77
Q

Alicia PS #1

3

A

See key

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77
Q

SP2013 MT1

1a

A

See solutions

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78
Q

CH. 11 Recommended Problems

30b

A

See CH. 11 Recommended Probs Key

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80
Q

CH. 11 Recommended Problems

30e

A

See CH. 11 Recommended Probs Key

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81
Q

CH. 12 Recommended Probs

66f

A

See CH.12 Rec. Problem Solutions

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82
Q

See Alkene Nomenclature PS

18

A

See key

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83
Q

CH. 11 Recommended Problems

29c

A

See CH. 11 Recommended Probs Key

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84
Q

CH. 11 Recommended Problems

41c

A

See CH. 11 Recommended Probs Key

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84
Q

CH. 11 Recommended Problems

41f

A

See CH. 11 Recommended Probs Key

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85
Q

Amines

For the above FG, give the following:

  1. Wavenumber range
  2. Signal chracteristics
A
  1. 3250-3500 cm-1
  2. Broad, strong
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86
Q

CH. 12 Recommended Probs

35b

A

See CH.12 Rec. Problem Solutions

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87
Q

CH. 12 Recommended Probs

63a

A

See CH.12 Rec. Problem Solutions

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88
Q

See NMR Practice Problems

6

A

See key

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88
Q

CH. 11 Recommended Problems

29a

A

See CH. 11 Recommended Probs Key

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88
Q

CH. 11 Recommended Problems

34b

A

See CH. 11 Recommended Probs Key

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88
Q

SP2010 MT1

1b

A

See key

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89
Q

CH. 12 Recommended Probs

31

A

See CH.12 Rec. Problem Solutions

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90
Q

CH. 12 Recommended Probs

43c

A

See CH.12 Rec. Problem Solutions

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91
Q

CH. 12 Recommended Probs

42e

A

See CH.12 Rec. Problem Solutions

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91
Q

CH. 12 Recommended Probs

65e

A

See CH.12 Rec. Problem Solutions

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91
Q

SP2010 MT1

3b

A

See key

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92
Q

Alicia PS #1

1a

A

See key

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93
Q

CH. 12 Recommended Probs

40a

A

See CH.12 Rec. Problem Solutions

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95
Q

CH. 11 Recommended Problems

49a

A

See CH. 11 Recommended Probs Key

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96
Q

CH. 12 Recommended Probs

45m

A

See CH.12 Rec. Problem Solutions

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97
Q

See Alkene Nomenclature PS

7

A

See key

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98
Q

See Alkene Nomenclature PS

8

A

See key

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99
Q

CH. 12 Recommended Probs

57e

A

See CH.12 Rec. Problem Solutions

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99
Q

CH. 11 Recommended Problems

63b

A

See CH. 11 Recommended Probs Key

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99
Q

Alicia PS #1

2d

A

See key

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100
Q

What is the IR wavenumber range for Esters?

A

1735-1750 cm-1

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101
Q

CH. 12 Recommended Probs

46g

A

See CH.12 Rec. Problem Solutions

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102
Q

CH. 12 Recommended Probs

69

A

See CH.12 Rec. Problem Solutions

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103
Q

CH. 11 Recommended Problems

30f

A

See CH. 11 Recommended Probs Key

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105
Q

Explain how mass spectrometry can be used to detect the presence of isotopes.

A
  • Since mass spec can determine the mass of compounds (and individual molecules) it can also determine the ratio of masses.
  • By knowing the isotopic ratio of a compound in nature, you can compare to the relative ratios and masses of isotopes in compound to “match” the isotopes in the compound to the isotopes found in nature.
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107
Q

CH. 12 Recommended Probs

46b

A

See CH.12 Rec. Problem Solutions

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108
Q

CH. 12 Recommended Probs

37e

A

See CH.12 Rec. Problem Solutions

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109
Q

See NMR Practice Problems

5

A

See key

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110
Q

What is the IR wavenumber range for Nitriles?

A

2220-2260 cm-1

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112
Q

Workshop Spectroscopy Practice #1-26

7

A

See key

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113
Q

CH. 12 Recommended Probs

46l

A

See CH.12 Rec. Problem Solutions

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114
Q

What is the IR wavenumber range for the C=C bond of alkenes?

A

1620-1680 cm-1

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115
Q

SP2013 MT1

2a

A

See solutions

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116
Q

CH. 11 Recommended Problems

63

A

See CH. 11 Recommended Probs Key

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116
Q

Workshop Spectroscopy Practice #1-26

9

A

See key

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117
Q

What is the wavenumber range for Alkenes?

A

3050-3150 cm-1

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119
Q

See NMR Practice Problems

21

A

See key

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120
Q

SP2010 MT1

5

A

See key

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121
Q

Explain the difference in orientation between geminal, trans-vicinal, cis-vicinal, allylic, and alkane coupling in HNMR.

A
  • Geminal: two H’s attached to the same C in a C=C bond.
  • trans-vicinal: two H’s that are trans to each other across a C=C bond.
  • cis-vicinal: two H’s that are cis to each other across a C=C bond.
  • Allylic: one H attached to a C in a C=C bond, and one H attached to a C which is bonded to one side of the C=C bond (so a H attached to this –>C-C=C)\
  • Alkane: two H’s on either side of a C-C bond.
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121
Q

CH. 12 Recommended Probs

57f

A

See CH.12 Rec. Problem Solutions

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121
Q

CH. 11 Recommended Problems

34a

A

See CH. 11 Recommended Probs Key

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122
Q

See Alkene Nomenclature PS

11

A

See key

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124
Q

SP2010 MT1

7b

A

See key

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125
Q

CH. 11 Recommended Problems

41h

A

See CH. 11 Recommended Probs Key

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127
Q

CH. 12 Recommended Probs

35c

A

See CH.12 Rec. Problem Solutions

128
Q

CH. 11 Recommended Problems

38a

A

See CH. 11 Recommended Probs Key

130
Q

CH. 12 Recommended Probs

45g

A

See CH.12 Rec. Problem Solutions

131
Q

CH. 12 Recommended Probs

70b

A

See CH.12 Rec. Problem Solutions

132
Q

CH. 12 Recommended Probs

46k

A

See CH.12 Rec. Problem Solutions

133
Q

CH. 12 Recommended Probs

67b

A

See CH.12 Rec. Problem Solutions

134
Q

CH. 11 Recommended Problems

61d

A

See CH. 11 Recommended Probs Key

135
Q

CH. 11 Recommended Problems

61b

A

See CH. 11 Recommended Probs Key

135
Q

Workshop Spectroscopy Practice #1-26

22

A

See key

137
Q

See NMR Practice Problems

16

A

See key

138
Q

CH. 12 Recommended Probs

64c

A

See CH.12 Rec. Problem Solutions

139
Q

See NMR Practice Problems

10

A

See key

140
Q

CH. 12 Recommended Probs

70a

A

See CH.12 Rec. Problem Solutions

140
Q

SP2013 MT1

8

A

See solutions

141
Q

SP2013 MT1

6a

A

See solutions

142
Q

Workshop Spectroscopy Practice #1-26

12

A

See key

143
Q

See NMR Practice Problems

20

A

See key

143
Q

CH. 11 Recommended Problems

50

A

See CH. 11 Recommended Probs Key

144
Q

Give the HNMR chemical shift range typical of this FG

Alkyl (primary)

A

0.7-1.3 ppm

145
Q

CH. 12 Recommended Probs

43a

A

See CH.12 Rec. Problem Solutions

146
Q

CH. 12 Recommended Probs

65g

A

See CH.12 Rec. Problem Solutions

147
Q

CH. 12 Recommended Probs

60a

A

See CH.12 Rec. Problem Solutions

149
Q

CH. 12 Recommended Probs

66c

A

See CH.12 Rec. Problem Solutions

150
Q

CH. 11 Recommended Problems

55d

A

See CH. 11 Recommended Probs Key

151
Q

Workshop Spectroscopy Practice #1-26

21

A

See key

156
Q

See Alkene Nomenclature PS

14

A

See key

157
Q

CH. 12 Recommended Probs

53a

A

See CH.12 Rec. Problem Solutions

158
Q

SP2013 MT1

3d

A

See solutions

159
Q

CH. 11 Recommended Problems

32c

A

See CH. 11 Recommended Probs Key

160
Q

CH. 12 Recommended Probs

37b

A

See CH.12 Rec. Problem Solutions

160
Q

Workshop Spectroscopy Practice #1-26

3

A

See key

161
Q

CH. 12 Recommended Probs

38

A

See CH.12 Rec. Problem Solutions

162
Q

CH. 12 Recommended Probs

66d

A

See CH.12 Rec. Problem Solutions

163
Q

CH. 11 Recommended Problems

30a

A

See CH. 11 Recommended Probs Key

164
Q

CH. 12 Recommended Probs

58d

A

See CH.12 Rec. Problem Solutions

165
Q

CH. 11 Recommended Problems

61g

A

See CH. 11 Recommended Probs Key

166
Q

CH. 12 Recommended Probs

68

A

See CH.12 Rec. Problem Solutions

169
Q

SP2010 MT1

4

A

See key

170
Q

What is the IR wavenumber range for Alkanes?

A

2850-3000 cm-1

171
Q

CH. 12 Recommended Probs

44c

A

See CH.12 Rec. Problem Solutions

172
Q

CH. 12 Recommended Probs

45c

A

See CH.12 Rec. Problem Solutions

173
Q

CH. 12 Recommended Probs

43d

A

See CH.12 Rec. Problem Solutions

174
Q

CH. 11 Recommended Problems

39

A

See CH. 11 Recommended Probs Key

175
Q

CH. 11 Recommended Problems

49c

A

See CH. 11 Recommended Probs Key

176
Q

CH. 12 Recommended Probs

45d

A

See CH.12 Rec. Problem Solutions

177
Q

CH. 11 Recommended Problems

34e

A

See CH. 11 Recommended Probs Key

178
Q

CH. 11 Recommended Problems

38c

A

See CH. 11 Recommended Probs Key

181
Q

CH. 12 Recommended Probs

43b

A

See CH.12 Rec. Problem Solutions

182
Q

CH. 12 Recommended Probs

45b

A

See CH.12 Rec. Problem Solutions

183
Q

CH. 12 Recommended Probs

46f

A

See CH.12 Rec. Problem Solutions

184
Q

CH. 12 Recommended Probs

51

A

See CH.12 Rec. Problem Solutions

185
Q

CH. 12 Recommended Probs

65f

A

See CH.12 Rec. Problem Solutions

186
Q

CH. 11 Recommended Problems

41e

A

See CH. 11 Recommended Probs Key

187
Q

CH. 12 Recommended Probs

59c

A

See CH.12 Rec. Problem Solutions

188
Q

CH. 11 Recommended Problems

46a

A

See CH. 11 Recommended Probs Key

191
Q

-CCH Alkynes

For the above FG, give the following

  1. Wavenumber length
  2. Signal characteristics
A
  1. 3260-3330 cm-1
  2. Sharp
192
Q

CH. 12 Recommended Probs

49h

A

See CH.12 Rec. Problem Solutions

193
Q

Workshop Spectroscopy Practice #1-26

25

A

See key

196
Q

CH. 12 Recommended Probs

49j

A

See CH.12 Rec. Problem Solutions

197
Q

SP2013 MT1

7c

A

See solutions

198
Q

CH. 12 Recommended Probs

49k

A

See CH.12 Rec. Problem Solutions

199
Q

CH. 12 Recommended Probs

66g

A

See CH.12 Rec. Problem Solutions

200
Q

Workshop Spectroscopy Practice #1-26

20

A

See key

201
Q

CH. 12 Recommended Probs

63d

A

See CH.12 Rec. Problem Solutions

202
Q

SP2010 MT1

1e

A

See key

204
Q

CH. 12 Recommended Probs

45l

A

See CH.12 Rec. Problem Solutions

205
Q

CH. 12 Recommended Probs

46m

A

See CH.12 Rec. Problem Solutions

206
Q

CH. 11 Recommended Problems

51c

A

See CH. 11 Recommended Probs Key

207
Q

CH. 11 Recommended Problems

61e

A

See CH. 11 Recommended Probs Key

208
Q

CH. 11 Recommended Problems

49b

A

See CH. 11 Recommended Probs Key

210
Q

What is the IR wavenumber range for Acyl halides?

A

1790-1815 cm-1

211
Q

What is the IR wavenumber range for Amides?

A

1650-1690 cm-1

212
Q

CH. 12 Recommended Probs

71

A

See CH.12 Rec. Problem Solutions

213
Q

SP2010 MT1

3f

A

See key

214
Q

CH. 12 Recommended Probs

63b

A

See CH.12 Rec. Problem Solutions

215
Q

CH. 12 Recommended Probs

67a

A

See CH.12 Rec. Problem Solutions

215
Q

Workshop Spectroscopy Practice #1-26

10

A

See key

215
Q

Workshop Spectroscopy Practice #1-26

15

A

See key

216
Q

SP2010 MT1

1c

A

See key

217
Q

CH. 11 Recommended Problems

31c

A

See CH. 11 Recommended Probs Key

218
Q

CH. 12 Recommended Probs

63e

A

See CH.12 Rec. Problem Solutions

219
Q

See Properties of Alkenes & pi-bonds

5

A

See key

219
Q

CH. 11 Recommended Problems

35

A

See CH. 11 Recommended Probs Key

220
Q

CH. 12 Recommended Probs

46e

A

See CH.12 Rec. Problem Solutions

222
Q

CH. 12 Recommended Probs

49p

A

See CH.12 Rec. Problem Solutions

223
Q

CH. 12 Recommended Probs

53d

A

See CH.12 Rec. Problem Solutions

224
Q

CH. 12 Recommended Probs

66h

A

See CH.12 Rec. Problem Solutions

225
Q

SP2013 MT1

3c

A

See solutions

226
Q

CH. 11 Recommended Problems

28

A

See CH. 11 Recommended Probs Key

228
Q

See Alkene Nomenclature PS

9

A

See key

229
Q

Workshop Spectroscopy Practice #1-26

4

A

See key

230
Q

Workshop Spectroscopy Practice #1-26

5

A

See key

231
Q

See NMR Practice Problems

18

A

See key

233
Q

See NMR Practice Problems

12

A

See key

236
Q

Give the HNMR chemical shift range typical of this FG

Alkyl (secondary)

A

1.2-1.6 ppm

237
Q

CH. 11 Recommended Problems

61c

A

See CH. 11 Recommended Probs Key

238
Q

CH. 12 Recommended Probs

53b

A

See CH.12 Rec. Problem Solutions

239
Q

CH. 11 Recommended Problems

66a

A

See CH. 11 Recommended Probs Key

240
Q

CH. 11 Recommended Problems

66d

A

See CH. 11 Recommended Probs Key

242
Q

CH. 12 Recommended Probs

45j

A

See CH.12 Rec. Problem Solutions

243
Q

Workshop Spectroscopy Practice #1-26

14

A

See key

244
Q

CH. 12 Recommended Probs

61

A

See CH.12 Rec. Problem Solutions

247
Q

What three things does mass spectrometry determine?

A
  1. Mass
  2. Fragmentation
  3. Presence of isotopes
248
Q

CH. 11 Recommended Problems

31a

A

See CH. 11 Recommended Probs Key

251
Q

CH. 12 Recommended Probs

35a

A

See CH.12 Rec. Problem Solutions

252
Q

How do the polarities of -cis and -trans alkenes compare?

A
  • cis* alkenes are mor polar than trans alkenes because the dipole moments of trans alkenes cancel each other out due to them being in opposite directions.
  • cis* alkenes by contrast have both their dipole moments going away the C=C bond, creating a net dipole moment.
253
Q

Workshop Spectroscopy Practice #1-26

24

A

See key

254
Q

What causes alkenes to be so downshifted (i.e. deshielded)?

A
  • Applying a magnetic field to an alkene causes electrons to circle the magnetic field lines in one direction.
  • The pi-bond of an alkene creates an addt’l local magnetic field reinforcing the external field created by the applied magnetic field.
  • This causes the extra shift & deshielding on the alkene protons.
256
Q

Ex. 118B (Workshop Spectroscopy Problem)

A

See key

257
Q

SP2010 MT1

1d

A

See key

258
Q

SP2013 MT1

2c

A

See solutions

261
Q

See Alkene Nomenclature PS

5

A

See key

262
Q

See NMR Practice Problems

4

A

See key

263
Q

CH. 11 Recommended Problems

29e

A

See CH. 11 Recommended Probs Key

264
Q

Allylic and geminal coupling in alkenes have the same Hz range. How can you tell them apart?

A

Geminal coupling only occurs in doublets (d); allylic can occur in doublet (d), triplet (t) or quartet (q) patterns.

So if you see a coupling pattern of 0-3 Hz with a triplet or quartet, you would know it was a geminal coupling.

267
Q

CH. 12 Recommended Probs

42d

A

See CH.12 Rec. Problem Solutions

268
Q

CH. 12 Recommended Probs

45n

A

See CH.12 Rec. Problem Solutions

269
Q

CH. 11 Recommended Problems

38b

A

See CH. 11 Recommended Probs Key

270
Q

CH. 12 Recommended Probs

49e

A

See CH.12 Rec. Problem Solutions

273
Q

See Alkene Nomenclature PS

17

A

See key

274
Q

CH. 12 Recommended Probs

49n

A

See CH.12 Rec. Problem Solutions

275
Q

CH. 12 Recommended Probs

66e

A

See CH.12 Rec. Problem Solutions

276
Q

CH. 11 Recommended Problems

63c

A

See CH. 11 Recommended Probs Key

277
Q

CH. 11 Recommended Problems

37b

A

See CH. 11 Recommended Probs Key

279
Q

Give the HNMR chemical shift range typical of this FG

Formyl (XCHO)

A

8-8.5 ppm

280
Q

CH. 11 Recommended Problems

41a

A

See CH. 11 Recommended Probs Key

283
Q

See NMR Practice Problems

1

A

See key

284
Q

CH. 12 Recommended Probs

43f

A

See CH.12 Rec. Problem Solutions

285
Q

SP2010 MT1

3a

A

See key

286
Q

SP2013 MT1

1b

A

See solutions

287
Q

Alicia PS #1

2a

A

See key

288
Q

See NMR Practice Problems

2

A

See key

289
Q

Carboxylic acids

For the above FG, give the following:

  1. Wavenumber range
  2. Signal characteristics
A
  1. 2500-3100 cm-1
  2. Broad, strong
290
Q

CH. 12 Recommended Probs

40d

A

See CH.12 Rec. Problem Solutions

291
Q

See Alkene Nomenclature PS

15

A

See key

292
Q

SP2013 MT1

1d

A

See solutions

293
Q

SP2010 MT1

3h

A

See key

294
Q

CH. 12 Recommended Probs

45k

A

See CH.12 Rec. Problem Solutions

296
Q

See Alkene Nomenclature PS

10

A

See key

297
Q

What is the IR wavenumber range for Aldehydes?

A

2850 & 2750 cm-1

299
Q

See Properties of Alkenes & pi-bonds

4

A

See key

300
Q

See NMR Practice Problems

17

A

See key

301
Q

CH. 12 Recommended Probs

37c

A

See CH.12 Rec. Problem Solutions

302
Q

CH. 12 Recommended Probs

65d

A

See CH.12 Rec. Problem Solutions

303
Q

Workshop Spectroscopy Practice #1-26

6

A

See key

305
Q

CH. 12 Recommended Probs

65c

A

See CH.12 Rec. Problem Solutions

306
Q

See NMR Practice Problems

9

A

See key

307
Q

SP2013 MT1

7a

A

See solutions

309
Q

See NMR Practice Problems

24

A

See key

310
Q

CH. 12 Recommended Probs

58a

A

See CH.12 Rec. Problem Solutions

311
Q

Explain how mass spectrometry works, and how it differs from spectroscopy.

A
  • Compound is exposed to ionizing radiation (e.g. X-Rays) that removes electrons, creating ions of the compound.
  • Ionized molecules are accelerated through a tube, where they are exposed to a magnetic field.
  • Like charges repel, so the charged ions are deflected by the charge.
  • Since heavier compounds are not as easily moved, the amount of deflection can be used to determine the mass of the compound.
312
Q

CH. 12 Recommended Probs

45i

A

See CH.12 Rec. Problem Solutions

313
Q

CH. 12 Recommended Probs

45f

A

See CH.12 Rec. Problem Solutions

314
Q

CH. 12 Recommended Probs

65b

A

See CH.12 Rec. Problem Solutions

315
Q

CH. 11 Recommended Problems

42

A

See CH. 11 Recommended Probs Key

316
Q

CH. 11 Recommended Problems

48

A

See CH. 11 Recommended Probs Key

317
Q

SP2013 MT1

3e

A

See solutions

318
Q

CH. 12 Recommended Probs

46c

A

See CH.12 Rec. Problem Solutions

319
Q

SP2010 MT1

6

A

See key

320
Q

What is the IR wavenumber range for Anhydrides?

A

1740-1790 cm-1 and 1800-1850 cm-1

323
Q

Give the HNMR chemical shift range typical of this FG

Internal alkene

A

5.2-6.0 ppm

324
Q

Workshop Spectroscopy Practice #1-26

18

A

See key

325
Q

SP2013 MT1

1e

A

See solutions

326
Q

See Alkene Nomenclature PS

13

A

See key

327
Q

See NMR Practice Problems

25

A

See key

328
Q

CH. 11 Recommended Problems

65

A

See CH. 11 Recommended Probs Key

329
Q

Give the HNMR chemical shift range typical of this FG

Allylic

A

1.6-2.2 ppm

329
Q

CH. 12 Recommended Probs

58c

A

See CH.12 Rec. Problem Solutions

331
Q

Give the HNMR chemical shift range typical of this FG

Next to C=O

A

2-2.5 ppm

332
Q

CH. 12 Recommended Probs

53c

A

See CH.12 Rec. Problem Solutions

333
Q

CH. 12 Recommended Probs

40b

A

See CH.12 Rec. Problem Solutions

334
Q

SP2013 MT1

3g

A

See solutions

335
Q

CH. 12 Recommended Probs

44d

A

See CH.12 Rec. Problem Solutions

336
Q

Workshop Spectroscopy Practice #1-26

13

A

See key

337
Q
  1. Which bond is stronger, sigma bonds or pi bonds?
  2. Why?
A
  1. Sigma bonds
  2. Sigma bonds have better overlap (end-to-end), while pi bonds have side-side overlap and have less contact overall.
340
Q

CH. 12 Recommended Probs

41b

A

See CH.12 Rec. Problem Solutions

341
Q

See NMR Practice Problems

8

A

See key

342
Q

What is the IR wavenumber range and typical value for Aldehydes?

A

1690-1750 cm-1, usually 1735 cm-1

343
Q

Workshop Spectroscopy Practice #1-26

16

A

See key

344
Q

Give the HNMR chemical shift range typical of this FG

Fluoroalkane

A

4.3-5.0 ppm

345
Q

What is the IR wavenumber range for a H attached to a C=C bond (alkene)?

A

~3050-3150 cm-1

346
Q

CH. 12 Recommended Probs

37a

A

See CH.12 Rec. Problem Solutions

347
Q

CH. 12 Recommended Probs

66a

A

See CH.12 Rec. Problem Solutions

348
Q

CH. 11 Recommended Problems

61h

A

See CH. 11 Recommended Probs Key

349
Q

CH. 11 Recommended Problems

57

A

See CH. 11 Recommended Probs Key

350
Q

CH. 12 Recommended Probs

46a

A

See CH.12 Rec. Problem Solutions

351
Q

See NMR Practice Problems

7

A

See key

352
Q

Give the HNMR chemical shift range typical of this FG

Alkyl (tertiary)

A

1.4-1.8 ppm

353
Q

Give the HNMR chemical shift range typical of this FG

Terminal alkene

A

4.6-5.2 ppm

354
Q

CH. 11 Recommended Problems

61f

A

See CH. 11 Recommended Probs Key

355
Q

If alkenes have shorter and stronger C-H bonds than alkanes, then why are they more acidic?

A

Due to the hybridization. Alkenes are sp2 hybridized, meaning that the orbitals have more s character (1/3) compared to alkanes (1/4).

Remember, s orbitals are spherical and hang out near the C in the C-H bond. If the hybridized orbital has more s character, than the electrons will remain closer to the C atom, making it easier for the H+ proton to leave.

356
Q

SP2010 MT1

8

A

See key

357
Q

CH. 12 Recommended Probs

32

A

See CH.12 Rec. Problem Solutions

358
Q

CH. 12 Recommended Probs

42b

A

See CH.12 Rec. Problem Solutions

360
Q

What is the IR wavenumber range for Carboxylic acid carbonyl groups?

A

1710-1760 cm-1

361
Q

CH. 11 Recommended Problems

30h

A

See CH. 11 Recommended Probs Key

363
Q

CH. 12 Recommended Probs

37d

A

See CH.12 Rec. Problem Solutions

364
Q

CH. 12 Recommended Probs

36

A

See CH.12 Rec. Problem Solutions

365
Q

CH. 12 Recommended Probs

46h

A

See CH.12 Rec. Problem Solutions

366
Q

CH. 11 Recommended Problems

41d

A

See CH. 11 Recommended Probs Key

367
Q

CH. 12 Recommended Probs

57d

A

See CH.12 Rec. Problem Solutions

368
Q

Alicia PS #1

2f

A

See key

369
Q

SP2013 MT1

7b

A

See solutions

370
Q

SP2013 MT1

5

A

See solutions

371
Q

CH. 11 Recommended Problems

63d

A

See CH. 11 Recommended Probs Key

372
Q

CH. 12 Recommended Probs

46n

A

See CH.12 Rec. Problem Solutions

373
Q

SP2013 MT1

6b

A

See solutions

374
Q

CH. 12 Recommended Probs

46i

A

See CH.12 Rec. Problem Solutions

376
Q

What is the IR wavenumber range and typical value for Ketones?

A

1690-1750 cm-1, usually 1715 cm-1

377
Q

SP2013 MT1

1c

A

See solutions

378
Q

SP2013 MT1

3f

A

See solutions

379
Q

SP2010 MT1

7a

A

See key

380
Q

See NMR Practice Problems

14

A

See key

381
Q

Give the HNMR chemical shift range typical of this FG

Alkyne

A

1.7-3.1 ppm

382
Q

Give the HNMR chemical shift range typical of this FG

Aldehyde (R-CHO)

A

9.5-10.0 ppm

383
Q

CH. 12 Recommended Probs

44a

A

See CH.12 Rec. Problem Solutions

384
Q

CH. 12 Recommended Probs

45h

A

See CH.12 Rec. Problem Solutions

385
Q

CH. 11 Recommended Problems

63e

A

See CH. 11 Recommended Probs Key

386
Q

See Properties of Alkenes & pi-bonds

3

A

See key

387
Q

CH. 11 Recommended Problems

51b

A

See CH. 11 Recommended Probs Key

388
Q

SP2010 MT1

2g

A

See key

389
Q

CH. 11 Recommended Problems

67

A

See CH. 11 Recommended Probs Key

390
Q

CH. 12 Recommended Probs

46o

A

See CH.12 Rec. Problem Solutions

391
Q

CH. 11 Recommended Problems

66c

A

See CH. 11 Recommended Probs Key

392
Q

CH. 11 Recommended Problems

37a

A

See CH. 11 Recommended Probs Key

393
Q

CH. 11 Recommended Problems

41b

A

See CH. 11 Recommended Probs Key

394
Q

See NMR Practice Problems

26

A

See key

395
Q

CH. 11 Recommended Problems

51d

A

See CH. 11 Recommended Probs Key

396
Q

CH. 11 Recommended Problems

62a

A

See CH. 11 Recommended Probs Key

397
Q

CH. 11 Recommended Problems

38d

A

See CH. 11 Recommended Probs Key

398
Q

CH. 12 Recommended Probs

43e

A

See CH.12 Rec. Problem Solutions

399
Q

CH. 11 Recommended Problems

64

A

See CH. 11 Recommended Probs Key

400
Q

Workshop Spectroscopy Practice #1-26

17

A

See key

401
Q

See Alkene Nomenclature PS

4

A

See key

402
Q

Give the HNMR chemical shift range typical of this FG

Amines

A

2.4-3.5 ppm

403
Q

CH. 12 Recommended Probs

45q

A

See CH.12 Rec. Problem Solutions

404
Q

CH. 12 Recommended Probs

60c

A

See CH.12 Rec. Problem Solutions

405
Q

CH. 11 Recommended Problems

46b

A

See CH. 11 Recommended Probs Key

406
Q

Ch. 12 Recommended Probs

54a

A

See key

407
Q

Ch. 12 Recommended Probs

54b

A

See key

408
Q

Ch. 12 Recommended Probs

54c

A

See key

409
Q

Ch. 12 Recommended Probs

54d

A

See key

410
Q

Ch. 12 Recommended Probs

54e

A

See key

411
Q

Ch. 12 Recommended Probs

55a

A

See key

412
Q

Ch. 12 Recommended Probs

55b

A

See key

413
Q

Ch. 12 Recommended Probs

55c

A

See key

414
Q

Ch. 12 Recommended Probs

55d

A

See key

415
Q

Ch. 12 Recommended Probs

55e

A

See key

416
Q

CH. 11 Recommended Problems

30g

A

See CH. 11 Recommended Probs Key

417
Q

CH. 11 Recommended Problems

32b

A

See CH. 11 Recommended Probs Key

418
Q

Workshop Spectroscopy Practice #1-26

1

A

See key

CHE 118B: Organic Chemistry (5 decks)

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